Polycyclic nitrogen-containing compounds

ABSTRACT

New and valuable polycyclic compounds which contain nitrogen-containing rings and have a strong action on plants, agents for influencing plant growth containing these compounds, and a method of influencing plant growth with these compounds.

This is a division of application Ser. No. 781,767, filed Mar. 28, 1977, now U.S. Pat. No. 4,189,434.

The present invention relates to new and valuable polycyclic compounds, processes for their manufacture, crop protection agents containing these compounds, and their use as crop protection agents.

We have found that compounds of the formula ##STR1## where A denotes the radical --N═N--, B denotes the radicals --SO₂ --, ##STR2## --S--, C denotes the radicals --N═N-- or ##STR3## n denotes one of the integers 0 and 1, m denotes one of the integers 0 and 1, and R¹ denotes hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms, alkynyl of 2 to 30 carbon atoms (preferably alkyl of 1 to 18 carbon atoms)--all of which may be linear or branched, cyclic or acyclic--, phenyl, naphthyl, or a more highly condensed aromatic radical, a heterocyclic radical with one or more hetero atoms (O, N, S), or aralkyl, it being possible for the aromatic radical to be substituted by a heterocycle, the abovementioned radicals, apart from hydrogen, being unsubstituted or mono- or polysubstituted by halogen (F, Cl, Br, I) or pseudo-halogen (CN, SCN), ##STR4## primary, secondary or tertiary alkyl, haloalkyl, haloalkoxy, haloalkylmercapto, or the radical ##STR5## Alk denoting alkyl and Ar denoting an aromatic radical, and R¹ may additionally denote, when m is 0, (Alk, Ar)₃ Si--, (Alk, Ar)₃ Sn-- and, when m is 1, --OAlk(Ar), --SAlk(Ar), the radical ##STR6## or --N(Alk,Ar)₂, and R² and R³ are identical or different and each denotes (B)_(m) --R⁴, R⁴ having the same meanings as R¹, and salts of these compounds, have a strong biological action on plants.

It is known to prepare compounds III-V, where R═CH₃ -- and C₂ H₅ --, by the following route: reaction of quadricyclane with azodicarboxylic acid esters (II) to give III, which is converted to IV by saponification and decarboxylation and oxidized, without isolation of IV, by CuCl₂ to the Cu^(I) complex of the azo compound V (JACS, 91, 5668, 1969). ##STR7##

Compound VI is obtained by partial saponification and decarboxylation of III.

The active ingredients according to the invention may be prepared as follows:

1. Preparation of the compounds described in Examples 1 and 2 and the tables relating thereto. Reaction of compounds III-VI with alkyl, aryl, aralkyl, sulfonyl, silyl, stannyl or heterocyclic azides or diazides synthesized by known methods (Houben-Weyl, 10/3, 777).

The reaction takes place in an indifferent solvent, e.g., petroleum ether, benzene, xylene, methylene chloride, chloroform, chlorobenzene, ether, tetrahydrofuran, dioxane, dimethylformamide and mixture of solvents, such as dioxane/water, the solvent depending on the solubility of the azide employed, at from -20° to +180° C., preferably +20° to 120° C. The reaction products precipitate out from the reaction solution either on cooling or, if polar solvents are used, upon addition of non-polar solvents, or may be obtained by concentrating the solution.

During the reaction, Δ² -1,2,3-triazoline derivatives are formed, some of which, e.g., sulfonyl azides or azides in which the azide group is in conjugation with strongly electronegative substituents, already convert under the reaction conditions to exo- and/or endo-aziridine derivatives by elimination of nitrogen.

The addition of silyl azides to the C═C double bond gives N-silyl-Δ² -1,2,3-triazoline derivatives from which the corresponding N-H-Δ² -1,2,3-triazoline derivatives are formed upon treatment with ethanol/ligroin.

2. Preparation of the compounds described in Examples 3 and 4 and the tables relating thereto. Elimination of nitrogen from the Δ² -1,2,3-triazoline compounds to give the corresponding aziridine derivatives.

The elimination takes place in the abovementioned solvents either upon heating at from 90° to 140° C. or, after addition of acid catalysts, at from 20° to 80° C. Examples of suitable catalysts are acids (e.g., sulfuric acid, acetic acid, trifluoroacetic acid) and insoluble carrier substances containing acidic groups (e.g., ion exchangers).

3. Preparation of the compounds described in Example 5 and the table relating thereto. Reaction of N--H--Δ² -1,2,3-triazoline or N--H-aziridine derivatives with carboxylic or thiocarboxylic acid halides, carboxylic acid anhydrides, chlorocarbonates, thiochlorocarbonates, phosgene, sulfonyl halides, sulfenyl halides, alkyl halides, alkenyl halides, alkynyl halides, aralkyl halides, aldehydes, ketones, isocyanates, mustard oils, and carbamoyl and thiocarbamoyl halides, the corresponding N-substituted triazoline and aziridine derivatives being formed either by elimination of hydrogen halide or by addition of the N-H group to the C═O or C═N double bond.

The reactions are carried out in known manner in inert solvents and usually in the presence of bases, e.g., tertiary amines, alkali metal carbonates or bicarbonates, sodium methylate, alkali metal hydroxides, etc., at from 20° to 100° C.

4. The reaction of compounds IV and VI with the substances listed under (3) gives the corresponding N-substituted and N,N'-disubstituted derivatives (Example 6), which are then reacted as described above under (1) and (2) (Example 2, 4).

5. The reaction of quadricyclane with alkyl, aryl or aralkyl azodicarboxylic acid diesters gives the corresponding N,N'-disubstituted derivatives (Example 6), which are then reacted as described above under (1) and (2) (Example 2, 4).

Generally, the compounds may be prepared by any of the processes given under (1), (2) and (3) above. However, the process for which the individual examples and tables are given is usually the most advantageous of the various methods possible.

The structure of the active ingredients was confirmed by nmr, infrared and mass spectroscopy or ultimate analysis.

The melting points given are uncorrected.

EXAMPLE 1 ##STR8##

72 Parts (by weight) of compound V and 92 parts of p-chlorophenylazide are heated in 240 parts of benzene for 5 hours at 80° C. After the mixture has cooled to room temperature, the Δ² -1,2,3-triazoline derivative which has formed is suction filtered and washed with 50 parts of petroleum ether; yield: 148 parts (90% of theory); m.p.: 192°-193° C. (decomposes). ##STR9##

12 Parts of V and 25 parts of 2-hydroxy-3-azido-5-chlorobenzenesulfonic acid are heated in 500 parts of dioxane/water (4:1) for 8 hours at 80° C. After the solvent has been distilled off in vacuo at 25 mbars, the residue is washed (digested) with 500 parts of benzene; yield: 32 parts (93% of theory); m.p.: 135° C. (decomposes). ##STR10##

3 Parts of V and 8.1 parts of perfluorobutylsulfonylazide are stirred in 15 parts of benzene for 20 hours at room temperature. After the benzene has been distilled off at 50 mbars, the residue is digested with 50 parts of petroleum ether; yield: 9 parts (86% of theory); m.p.: 115° C. (decomposes).

The following compounds were prepared analogously:

    ______________________________________                                          ##STR11##                                                                                                    m.p.                                            R.sup.1            n     m     [°C.]                                    ______________________________________                                         H                  1     0     136  (decomposes)                               CH.sub.3           0     1     135  (decomposes)                               C.sub.3 H.sub.7    1     0     56   (decomposes)                               C.sub.8 H.sub.17   0     1     96   (decomposes)                               C.sub.12 H.sub.25  1     0     63   (decomposes)                                ##STR12##         1     0     100                                             CH.sub.2COOCH.sub.3                                                                               1     0     76                                              CH.sub.2CN         1     0     94   (decomposes)                                ##STR13##         1     0     76                                              CH.sub.2CH.sub.2N(C.sub.3 H.sub.7).sub.2                                                          1     0     54                                              (CH.sub.2).sub.3N(C.sub.2 H.sub.5).sub.2                                                          1     0     16                                               ##STR14##         1     0     62                                              CH.sub.2C.sub.6 H.sub.5                                                                           1     0     100                                              ##STR15##         1     0     88   (decomposes)                                ##STR16##         1     0     164  (decomposes)                                ##STR17##         1     0     170  (decomposes)                                ##STR18##         1     0     159  (decomposes)                                ##STR19##         1     0     191  (decomposes)                                ##STR20##         1     0     124  (decomposes)                                ##STR21##         1     0     144  (decomposes)                               C.sub.6 H.sub.5    1     0     149  (decomposes)                               C.sub.6 H.sub.5    0     1     119  (decomposes)                                ##STR22##         1     0     159  (decomposes)                                ##STR23##         0     1     135  (decomposes)                               p-BrC.sub.6 H.sub.4                                                                               1     0     185  (decomposes)                               p-ClC.sub.6 H.sub.4                                                                               0     1     125  (decomposes)                               p-NO.sub.2C.sub.6 H.sub.4                                                                         1     0     192  (decomposes)                               p-CH.sub.3 OC.sub.6 H.sub.4                                                                       1     0     153  (decomposes)                               p-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     159  (decomposes)                               p-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     126  (decomposes)                                ##STR24##         1     0     187  (decomposes)                               p-FC.sub.6 H.sub.4 1     0     156  (decomposes)                               p-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                                  1     0     168  (decomposes)                               p-HOOCC.sub.6 H.sub.4                                                                             1     0     182  (decomposes)                                ##STR25##         1     0     216  (decomposes)                               p(C.sub.2 H.sub.5).sub.2 NC.sub.6 H.sub.4                                                         1     0     123  (decomposes)                               o-ClC.sub.6 H.sub.4                                                                               1     0     120  (decomposes)                               o-BrC.sub.6 H.sub.4                                                                               1     0     102  (decomposes)                               o-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     105  (decomposes)                               o-NO.sub.2C.sub.6 H.sub.4                                                                         1     0     168  (decomposes)                               o-NO.sub.2C.sub.6 H.sub.4                                                                         0     1     185  (decomposes)                               m-ClC.sub.6 H.sub.4                                                                               1     0     152  (decomposes)                               m-BrC.sub.6 H.sub.4                                                                               1     0     172  (decomposes)                               m-NO.sub.2C.sub.6 H.sub.4                                                                         1     0     193  (decomposes)                               m-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     151  (decomposes)                               m-CF.sub.3C.sub.6 H.sub.4                                                                         1     0     145  (decomposes)                               m-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                                  1     0     127  (decomposes)                                ##STR26##         1     0     182  (decomposes)                                ##STR27##         1     0     143  (decomposes)                                ##STR28##         1     0     113  (decomposes)                                ##STR29##         1     0     162  (decomposes)                                ##STR30##         1     0     173  (decomposes)                                ##STR31##         1     0     141  (decomposes)                                ##STR32##         1     0     127  (decomposes)                                ##STR33##         1     0     152  (decomposes)                                ##STR34##         1     0     78   (decomposes)                                ##STR35##         1     0     186  (decomposes)                                ##STR36##         1     0     175  (decomposes)                                ##STR37##         1     0     129  (decomposes)                                ##STR38##         1     0     159  (decomposes)                                ##STR39##         1     0     168  (decomposes)                                ##STR40##         1     0     166  (decomposes)                                ##STR41##         1     0     168  (decomposes)                                ##STR42##         1     0     164  (decomposes)                                ##STR43##         1     0     191  (decomposes)                                ##STR44##         1     0     164  (decomposes)                                ##STR45##         1     0     131  (decomposes)                                ##STR46##         1     0     189  (decomposes)                                ##STR47##         0     0     187  (decomposes)                                ##STR48##         0     0     255  (decomposes)                                ##STR49##         0     0     150  (decomposes)                                ##STR50##         1     0     181  (decomposes)                                ##STR51##         1     0     136  (decomposes)                                ##STR52##         1     0     196  (decomposes)                                ##STR53##         1     0     184  (decomposes)                                ##STR54##         0     0     250  (decomposes)                                ##STR55##         1     0     136  (decomposes)                                ##STR56##         1     0     132  (decomposes)                                ##STR57##         1     0     184  (decomposes)                                ##STR58##         0     0     155  (decomposes)                                ##STR59##         1     0     60   (decomposes)                                ##STR60##         1     0     188  (decomposes)                                ##STR61##         0     0     150  (decomposes)                                ##STR62##         1     0     199  (decomposes)                                ##STR63##         0     0     211  (decomposes)                                ##STR64##         1     0     220  (decomposes)                                ##STR65##         1     0     147  (decomposes)                                ##STR66##         1     0     175  (decomposes)                                ##STR67##         1     0     183  (decomposes)                                ##STR68##         0     0     92   (decomposes)                                ##STR69##         1     0     214  (decomposes)                                ##STR70##         1     0     69   (decomposes)                                ##STR71##         1     0     138  (decomposes)                                ##STR72##         1     0     112  (decomposes)                                ##STR73##         1     0     160                                             ______________________________________                                    

EXAMPLE 2 ##STR74##

24 Parts of III and 20 parts of p-bromophenylazide are heated in 80 parts of benzene for 5 hours at 80° C. After the mixture has cooled to room temperature, the reaction product is suction filtered and washed with 50 parts of petroleum ether; yield: 38 parts (86% of theory); m.p.: 217°-218° C. (decomposes). ##STR75##

12 Parts of III and 9 parts of phenylsulfonylazide are heated in 100 parts of chlorobenzene for 6 hours at 100° C. After the solvent has been distilled off at 25 mbars, the residue is digested with 100 parts of petroleum ether; yield: 18 parts (97% of theory); m.p.: 146° C. (ethanol/ligroin).

Compounds in which R² and/or R³ denote H may also be present in the form of their salts, for instance as salts with mineral acids, e.g., as hydrochlorides.

The following compounds were prepared analogously:

    __________________________________________________________________________      ##STR76##                                                                                                                         m.p.                       R.sup.1       R.sup.2        R.sup.3           n m  [°C.]               __________________________________________________________________________     H             COOCH.sub.3    COOCH.sub.3       1 0  83 (decomposes)            CH.sub.3      "              "                 0 1  100                                                                               (decomposes)            C.sub.3 H.sub.7                                                                              "              "                 1 0  86 (decomposes)            CH.sub.2COOCH.sub.3                                                                          "              "                 1 0  169                                                                               (decomposes)            CH.sub.2C.sub.6 H.sub.5                                                                      "              "                 1 0  118                                                                               (decomposes)            C.sub.6 H.sub.5                                                                              "              "                 1 0  157                                                                               (decomposes)            C.sub.6 H.sub.5                                                                              COOC.sub.2 H.sub.5                                                                            COOC.sub.2 H.sub.5                                                                               1 0  125                                                                               (decomposes)             ##STR77##    H              H                 1 0  135                                                                               (decomposes)             ##STR78##    H              H                 1 0  129                                                                               (decomposes)             ##STR79##    .sup.++ H      COOCH.sub.3       1 0  138                                                                               (decomposes)             ##STR80##    .sup.++ H      COOCH.sub.3       1 0   85                                                                               (decomposes)             ##STR81##    COOCH.sub.3    COOCH.sub.3       1 0  212                                                                               (decomposes)            "             .sup.++COOCH.sub.3                                                                             ##STR82##        1 0  117                                                                               (decomposes)                           ##STR83##     COOCH.sub.3       1 0  229                                                                               (decomposes)            "                                                                                             ##STR84##     "                 1 0  217                                                                               (decomposes)            "                                                                                             ##STR85##     "                 1 0  113                                                                               (decomposes)            "                                                                                             ##STR86##     "                 1 0   84                                                                               (decomposes)            "             .sup.++SO.sub.2C.sub.6 H.sub.5                                                                "                 1 0  139                                                                               (decomposes)            "                                                                                             ##STR87##                                                                                     ##STR88##        1 0  210                                                                               (decomposes)            "             COOCH.sub.2C.sub.6 H.sub.5                                                                    COOCH.sub.2C.sub.6 H.sub.5                                                                       1 0  70 (decomposes)            "             COOC.sub.6 H.sub.5                                                                            COOC.sub.6 H.sub.5                                                                               1 0  173                                                                               (decomposes)            "             COOC.sub.3 H.sub.7                                                                            COOC.sub.3 H.sub.7                                                                               1 0  150                                                                               (decomposes)             ##STR89##    .sup.++COOCH.sub.3                                                                             ##STR90##        1 0  oil                         ##STR91##                   COOCH.sub.3       1 0  221                                                                               (decomposes)             ##STR92##    "              "                 1 0  197                                                                               (decomposes)             ##STR93##    "              "                 1 0  221                                                                               (decomposes)             ##STR94##    "              "                 1 0  88 (decomposes)             ##STR95##    "              "                 1 0  180                                                                               (decomposes)             ##STR96##    "              "                 1 0  163                                                                               (decomposes)             ##STR97##    "              "                 1 0  158                                                                               (decomposes)             ##STR98##    "              "                 1 0  206                                                                               (decomposes)             ##STR99##    "              "                 0 0  250                                                                               (decomposes)             ##STR100##   "              "                 1 0  181                                                                               (decomposes)             ##STR101##   .sup.++COOCH.sub.3                                                                             ##STR102##       1 0  156                                                                               (decomposes)             ##STR103##   COOCH.sub.3    COOCH.sub.3       0 1  120                                                                               (decomposes)             ##STR104##   H              H                 1 0  94                         __________________________________________________________________________      .sup.++ isomer mixture; R.sup.2 and R.sup.3 are interchangeable          

EXAMPLE 3 ##STR105##

10 Parts of the abovementioned Δ² -1,2,3-triazoline derivative and 3 parts of trifluoroacetic acid are stirred for 5 hours in 50 parts of methylene chloride at room temperature. After the solvent has been distilled off, the residue is digested with 30 parts of ether; yield: 8 parts (88% of theory); m.p.: 195° C. (decomposes) (benzene/ligroin). ##STR106##

4 Parts of the abovementioned Δ² -1,2,3-triazoline derivative is heated in 20 parts of dioxane for 6 hours at 100° C. After the solvent has been distilled off, the residue is digested with 10 parts of petroleum ether; yield: 3 parts (85% of theory); m.p.: 159° C. (decomposes) (ether/petroleum ether).

The following compounds were prepared analogously:

    ______________________________________                                          ##STR107##                                                                                                   m.p.                                            R.sup.1          m     B       [°C.]                                    ______________________________________                                         H                0     --      115                                             C.sub.6 H.sub.5  0     --      149                                              ##STR108##      1                                                                                     ##STR109##                                                                            80                                               ##STR110##      0     --      140                                              ##STR111##      0     --      179  (decomposes)                                ##STR112##      0     --      122  (decomposes)                                ##STR113##      0     --      126  (decomposes)                                ##STR114##      0     --      110  (decomposes)                                ##STR115##      0     --      212  (decomposes)                                ##STR116##      0     --      66                                               ##STR117##      0     --      169  (decomposes)                                ##STR118##      0     --      194  (decomposes)                                ##STR119##      0     --      203  (decomposes)                                ##STR120##      0     --      146                                             EXAMPLE 4                                                                       ##STR121##                                                                     ##STR122##                                                                    ______________________________________                                    

40 Parts of the N-(p-bromophenyl)-Δ² -1,2,3-triazoline derivative is heated in 800 parts of xylene for 24 hours at 140° C. After the solvent has been distilled off, the residue is digested with 100 parts of petroleum ether; yield: 35 parts (92% of theory); m.p.: 170° C. (decomposes) (benzene/ligroin).

The following compounds were prepared analogously:

    ______________________________________                                          ##STR123##                                                                    R.sup.1    R.sup.2    R.sup.3    m.p. (°C.)                             ______________________________________                                         C.sub.6 H.sub.5CH.sub.2                                                                   COOCH.sub.3                                                                               COOCH.sub.3                                                                               140  (decom-                                                                        poses)                                   C.sub.6 H.sub.5                                                                            "          "         187                                            "         COOC.sub.2 H.sub.5                                                                        COOC.sub.2 H.sub.5                                                                        109                                            ##STR124##                                                                               COOCH.sub.3                                                                               COOCH.sub.3                                                                               168                                            "         COOC.sub.6 H.sub.5                                                                        COOC.sub.6 H.sub.5                                                                        117                                            ##STR125##                                                                               COOCH.sub.3                                                                                "         174                                            ##STR126##                                                                                "          "         209                                            ##STR127##                                                                                "          "         153                                            ##STR128##                                                                               COOCH.sub.3                                                                               COOCH.sub.3                                                                               197                                            ##STR129##                                                                                "          "         175                                            ##STR130##                                                                                "          "         178                                            ##STR131##                                                                                "          "         190  (decom- poses)                            ##STR132##                                                                                "          "         258  (decom- poses)                           ______________________________________                                    

EXAMPLE 5 ##STR133##

10 Parts of the N-H-.sup.Δ2 -1,2,3-triazoline derivative and 2 parts of sodium methylate are stirred in 100 parts of tetrahydrofuran for 1 hour at room temperature. 8.6 parts of benzoyl chloride is then dripped in and the mixture stirred for a further two hours. After the precipitate has been removed by suction filtration, the solvent is distilled off at 50 mbars and the residue digested with 30 parts of ether; yield: 13 parts (80% of theory); m.p.: 117° C. (decomposes). ##STR134##

3 Parts of the N-H-aziridine derivative and 3 parts of triethylamine are dissolved in 50 parts of tetrahydrofuran. At 0° to 5° C. and while stirring, 3.9 parts of benzene sulfochloride is dripped in. After removal of the precipitated triethylammonium chloride by suction filtration, the solvent is distilled off. The residue is washed with 50 parts of water and dried; yield: 5.4 parts (88% of theory); m.p.: 154° C. (decomposes).

The following compounds were prepared analogously:

    __________________________________________________________________________      ##STR135##                                                                    R.sup.1              n m B   m.p. [°C.]                                 __________________________________________________________________________     OCH.sub.3            1 1                                                                                 ##STR136##                                                                        117 (decomposes)                                  OC.sub.3 H.sub.7     1 1                                                                                 ##STR137##                                                                        118 (decomposes)                                   ##STR138##          1 1                                                                                 ##STR139##                                                                        156 (decomposes)                                   ##STR140##          1 1                                                                                 ##STR141##                                                                        169 (decomposes)                                   ##STR142##          0 1                                                                                 ##STR143##                                                                        118 (decomposes)                                  N(CH.sub.3).sub.2    1 1                                                                                 ##STR144##                                                                        108 (decomposes)                                  CH.sub.3             1 1                                                                                 ##STR145##                                                                         79                                               HCCCH.sub.2          1 0 --   60                                                ##STR146##          1 0 --   66 (decomposes)                                   ##STR147##          1 0 --  159 (decomposes)                                   ##STR148##          1 1 S   164 (decomposes)                                   ##STR149##          1 1                                                                                 ##STR150##                                                                        270 (decomposes)                                   ##STR151##          1 1                                                                                 ##STR152##                                                                        155 (decomposes)                                  C.sub.6 H.sub.5NH    1 1                                                                                 ##STR153##                                                                        163 (decomposes)                                  __________________________________________________________________________

EXAMPLE 6

Preparation of the starting compounds ##STR154##

At 65° C. and while stirring, a solution of 35 parts of KOH in 60 parts of methanol is dripped into 60 parts of compound III and 50 parts of methanol. The reaction mixture is then stirred for a further 2 hours at 65° C. The solvent is subsequently distilled off at 50 mbars and the residue is extracted several times with a total of 1,200 parts of ether. After distilling off the ether, there is obtained 38 parts of compound VI (85% of theory; m.p. 94° C. from ligroin). ##STR155##

5 Parts of compound VI, 7 parts of p-chlorobromoacetophenone and 3 parts of soda are stirred in 150 parts of ether for 24 hours at 34° C. After suction filtration of the organic salts, the solvent and the residue are digested with 50 parts of petroleum ether; 9.5 parts (91% of theory); m.p.: 111° C. (benzene/ligroin).

C. 17 parts of compound VI and 8.7 parts of methyl mustard oil are heated in 200 parts of benzene for 5 hours at 80° C. After the solvent has been distilled off, the residue is digested with 100 parts of petroleum ether; yield: 25 parts (97% of theory); m.p.: 116° C. (ethanol/ligroin). ##STR156##

At 80° C., 40.5 parts of azodicarboxylic acid diisopropyl ester is dripped into 20 parts of quadricyclane in 100 parts of benzene. The mixture is then heated for 24 hours at 80° C. and the solvent subsequently removed at 50 mbars; yield: 58 parts (98% of theory) of an oil.

The compounds in which R² and/or R³ denote H may also be present in the form of their salts, for instance as salts with mineral acids, e.g., as hydrochlorides.

The following compounds were prepared analogously:

    __________________________________________________________________________      ##STR157##                                                                    R.sup.2            R.sup.3 m.p.                                                                              (°C.)                                     __________________________________________________________________________                         ##STR158##                                                                            163                                                                               (decomposes)                                     CH.sub.2COOCH.sub.3                                                                               COOCH.sub.3                                                                            76                                                  SO.sub.2C.sub.6 H.sub.5                                                                           "       130                                                  ##STR159##        "       128                                                  ##STR160##        "       141                                                  ##STR161##        "       164                                                                               (decomposes)                                      ##STR162##        "       128                                                  ##STR163##        "       b.p.                                                                              100/1 mbar                                        ##STR164##        "       73                                                   ##STR165##        "       75                                                   ##STR166##        "       oil                                                  ##STR167##        "       135                                                 C.sub.6 H.sub.5    C.sub.6 H.sub.5                                                                        98                                                  C.sub.6 H.sub.5CH.sub.2                                                                           C.sub.6 H.sub.5CH.sub.2                                                                oil                                                 __________________________________________________________________________

The compounds in Example 6 and the table were employed as starting compounds for active ingredient syntheses (cf. tables relating to Examples 2 and 4).

The new active ingredients have a strong biological action on plants, i.e., they influence plant growth, either by reducing the growth height, by changing the concentration of the plant constituents, or by destroying unwanted plants while not harming the crop plants.

Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, etc. and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenol polyglycol ethers, alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

There may be added to the compositions or individual active ingredients oils of various types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g., silicones), and growth regulators.

Examples of herbicidally active compounds with which the active ingredients according to the invention may be combined are as follows:

    ______________________________________                                          ##STR168##                                                                    R               R.sup.1                                                        ______________________________________                                          ##STR169##     NH.sub.2                                                        ##STR170##     NHCH.sub.3                                                      ##STR171##     NHCH.sub.3                                                      ##STR172##     NH.sub.2                                                        ##STR173##     NH.sub.2                                                        ##STR174##                                                                    R      R.sup.1   R.sup.2                                                       ______________________________________                                                 ##STR175##                                                                              H and salts                                                   H                                                                                      ##STR176##                                                                              Cl and salts                                                  H                                                                                      ##STR177##                                                                              F and salts                                                   H                                                                                      ##STR178##                                                                              CH.sub.3 and salts                                            Cl.sub.2 OCH.sub.3                                                                     ##STR179##                                                                              H and salts                                                    ##STR180##                                                                     ##STR181##                                                                    R.sup.1                                                                               R.sup.2   R.sup.3                                                       ______________________________________                                         CF.sub.3                                                                              nC.sub.3 H.sub.7                                                                         nC.sub.3 H.sub.7                                              CF.sub.3                                                                              nC.sub.3 H.sub.7                                                                         CH.sub.2CH.sub.2 Cl                                           SO.sub.2 NH.sub.2                                                                     nC.sub.3 H.sub.7                                                                         nC.sub.3 H.sub.7                                               ##STR182##                                                                    R.sup.1     R.sup.2                                                                               R.sup.3                                                     ______________________________________                                         CH.sub.3    H                                                                                      ##STR183##                                                  ##STR184## H      i-C.sub.3 H.sub.7                                            ##STR185## H                                                                                      ##STR186##                                                  ##STR187## H                                                                                      ##STR188##                                                  ##STR189## H      i-C.sub.3 H.sub.7                                            ##STR190## H      CH.sub.2CCCH.sub.2 Cl                                        ##STR191## H                                                                                      ##STR192##                                                  ##STR193## H      CH.sub.3                                                     ##STR194## H      CH.sub.3                                                     ##STR195##                                                                     ##STR196##                                                                    R.sup.1 R.sup.2                                                                               R.sup.3                                                         ______________________________________                                          ##STR197##                                                                            H      C.sub.2 H.sub.5                                                  ##STR198##                                                                            CH.sub. 3                                                                             CH.sub.3                                                         ##STR199##                                                                            H      CH.sub.3                                                         ##STR200##                                                                            H      C.sub.2 H.sub.5                                                  ##STR201##                                                                            H      CH.sub.3                                                         ##STR202##                                                                            H      C.sub.2 H.sub.5                                                  ##STR203##                                                                    R.sup.1 R.sup.2    R.sup.3                                                     ______________________________________                                         i-C.sub.3 H.sub.7                                                                      i-C.sub.3 H.sub.7                                                                         CH.sub.2CClCHCl                                             n-C.sub.3 H.sub.7                                                                      n-C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                             n-C.sub.3 H.sub.7                                                                      n-C.sub.3 H.sub.7                                                                         n-C.sub.3 H.sub.7                                           sec . C.sub.4 H.sub.9                                                                  sec . C.sub.4 H.sub.9                                                                     C.sub.2 H.sub.5                                             C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                            ##STR204##                                                  ##STR205##                                                                            C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                              ##STR206##                                                                            C.sub.2 H.sub.5                                                                           C.sub. 2 H.sub.5                                             ##STR207##                                                                     ##STR208##                                                                    ______________________________________                                         C.sub.2 H.sub.5                                                                n-C.sub.3 H.sub.7                                                               ##STR209##                                                                     ##STR210##                                                                    R.sup.1           X     Y       R.sup.2                                        ______________________________________                                         CH.sub.3          Cl    Cl      Na                                             Cl                Cl    Cl      Na                                             C.sub.2 H.sub.5   Cl    Cl      Na                                              ##STR211##       Cl    H       CH.sub.3                                        ##STR212##       H     H       H and salts                                     ##STR213##       H     Cl      NH.sub.4                                        ##STR214##       H     CH.sub.3                                                                               C.sub.2 H.sub.5                                 ##STR215##       H     CH.sub.3                                                                               CH.sub.3                                       "                 H     CH.sub.3                                                                               i-C.sub.3 H.sub.7                               ##STR216##       H     CH.sub.3                                                                                ##STR217##                                     ##STR218##       H     CH.sub.3                                                                               CH.sub.3                                        ##STR219##                                                                     ##STR220##                                                                     ##STR221##                                                                    R.sup.1                                                                               X      R.sup.2                                                          ______________________________________                                         i-C.sub.3 H.sub.7                                                                    Cl      C.sub.2 H.sub.5                                                  "     Cl                                                                                      ##STR222##                                                      "     Cl      i-C.sub.3 H.sub.7                                                C.sub.2 H.sub.5                                                                      Cl      C.sub.2 H.sub.5                                                  "     Cl      C(CH.sub.3).sub.2 CN                                             "     Cl                                                                                      ##STR223##                                                      "     Cl                                                                                      ##STR224##                                                       ##STR225##                                                                          Cl      (CH.sub.3).sub.2CH                                               "     Cl      tert . C.sub.4 H.sub.9                                           i-C.sub.3 H.sub.7                                                                    OCH.sub.3                                                                              i-C.sub.3 H.sub.7                                                "     SCH.sub.3                                                                              C.sub.3 H.sub.5                                                  C.sub.2 H.sub.5                                                                      SCH.sub.3                                                                              C.sub.2 H.sub.5                                                  "     SCH.sub.3                                                                              tert . C.sub.4 H.sub.9                                            ##STR226##                                                                    X       Y          R                                                           ______________________________________                                         CF.sub.3                                                                               H          CH.sub.3                                                    H       F          CH.sub.3                                                     ##STR227##                                                                    R.sup.1     R.sup.2        R.sup.3                                             ______________________________________                                          ##STR228##                                                                                 ##STR229##    CH.sub.2 Cl                                          ##STR230##                                                                                 ##STR231##    CH.sub.2 Cl                                          ##STR232## CH.sub.2CH.sub.2OCH.sub.3                                                                     CH.sub.2 Cl                                          ##STR233##  CH.sub.2OCH.sub.3                                                                            CH.sub.2 Cl                                         "            CH.sub.2OCH.sub.3                                                                            CH.sub.2 Cl                                         "            CH.sub.2OC.sub.4 H.sub.9 n                                                                   CH.sub.2 Cl                                          ##STR234##                                                                                  ##STR235##   CH.sub.2 Cl                                          ##STR236##  H             --                                                   ##STR237##  H                                                                                             ##STR238##                                         "            H             C.sub.2 H.sub.5                                      ##STR239##  H             C(CH.sub.3).sub.2C.sub.3 H.sub.7                     ##STR240##  H             CH.sub.3                                             ##STR241##  H             CH.sub.3                                             ##STR242##  H                                                                                             ##STR243##                                          ##STR244##                                                                     ##STR245##                                                                    X     X.sup.1 R                                                                ______________________________________                                         Br    Br      H and salts                                                      I     I       H and salts                                                      Br    Br                                                                                      ##STR246##                                                       ##STR247##                                                                    X = NO.sub.2                                                                   X = CN                                                                          ##STR248##                                                                    R    R.sup.1 R.sup.2 R.sup.3                                                   ______________________________________                                         Cl   Cl      Cl      H                                                         F    Cl      Cl      H                                                         Cl   Cl      H       H                                                         Cl   CF.sub.3                                                                               H       COOH                                                      Cl   Cl      H       COOCH.sub.3                                               NO.sub.2                                                                            CF.sub.3                                                                               H       H                                                         H    CF.sub.3                                                                               Cl      H                                                         H    CF.sub.3                                                                               Cl      OC.sub.2 H.sub.5                                          Cl   Cl      H       OCH.sub.3                                                  ##STR249##                                                                    R.sup.1       R.sup.2                                                                               R.sup.3                                                                               R.sup.4                                            ______________________________________                                          ##STR250##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR251##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR252##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR253##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR254##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR255##   H      CH.sub.3                                                                               ##STR256##                                         ##STR257##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR258##   H      CH.sub.3                                                                              OCH.sub.3                                           ##STR259##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR260##   H      CH.sub.3                                                                              OCH.sub.3                                           ##STR261##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR262##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR263##   H      CH.sub.3                                                                              OCH.sub.3                                           ##STR264##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR265##   H      CH.sub.3                                                                              OCH.sub.3                                           ##STR266##   H      CH.sub.3                                                                              OCH.sub.3                                           ##STR267##   H      CH.sub.3                                                                              CH.sub.3                                            ##STR268##   CH.sub.3                                                                              H      CH.sub.3                                            ##STR269##                                                                     ##STR270##                                                                     ##STR271##                                                                     ##STR272##                                                                    R       R.sup.1        R.sup.2                                                 ______________________________________                                         tert. C.sub.4 H.sub.9                                                                  NH.sub.2       SCH.sub.3                                                "                                                                                      ##STR273##    SCH.sub.3                                                ##STR274##                                                                            NH.sub.2       CH.sub.3                                                 ##STR275##                                                                    R.sup.1                                                                             R.sup.2         R.sup.3                                                   ______________________________________                                         CH.sub.3                                                                            Br              sec. C.sub.4 H.sub.9                                      CH.sub.3                                                                            Cl              tert. C.sub.4 H.sub.9                                     CH.sub.3                                                                            Cl                                                                                              ##STR276##                                                    CH.sub.2CH.sub.2CH.sub.2                                                                        ##STR277##                                                ##STR278##                                                                    R.sup.1                                                                              R.sup.2                                                                  ______________________________________                                         CH.sub.3                                                                             CH.sub.3                                                                 CH.sub.3                                                                              ##STR279##                                                               ##STR280##                                                                     ##STR281##                                                                    R.sup.1         R.sup.2   R.sup.3                                              ______________________________________                                          ##STR282##     sec. C.sub.4 H.sub.9                                                                     H                                                     "              tert. C.sub.4 H.sub.9                                                                    H                                                     "               "        CH.sub.3                                             H               CH.sub.3  H salts and esters                                   H               sec. C.sub.4 H.sub.9                                                                     H salts and esters                                   H               tert. C.sub.4 H.sub.9                                                                    Hsalts and esters                                    H                "        CH.sub.3 salts and esters                             ##STR283##                                                                    R.sup.1                                                                        ______________________________________                                          ##STR284##                                                                     ##STR285##                                                                     ##STR286##                                                                     ##STR287##                                                                     ##STR288##                                                                    R.sup.1                                                                             X                                                                         ______________________________________                                         H    CH.sub.3 OSO.sub.3                                                        Br   "                                                                         CH.sub.3                                                                            "                                                                         CH.sub.3                                                                            CF.sub.3 SO.sub.3                                                          ##STR289##                                                                     ##STR290##                                                                     ##STR291##                                                                     ##STR292##                                                                     ##STR293##                                                                     ##STR294##                                                                     ##STR295##                                                                     ##STR296##                                                                     ##STR297##                                                                     ##STR298##                                                                    R.sup.1                                                                             R.sup.2                                                                               R.sup.3                                                                               R.sup.4                                                     ______________________________________                                         H    Cl     NH.sub.2                                                                              Cl                                                          H    I      I      I                                                           Cl   H      Cl     OCH.sub.3                                                   Cl   Cl     H      Cl                                                          Cl   Cl     Cl     OCH.sub.3                                                    ##STR299##                                                                    R.sup.1  R.sup.2 R.sup.13                                                      ______________________________________                                          ##STR300##                                                                             H       H     salts, esters, amides                                   "        CH.sub.3                                                                               H     "                                                        ##STR301##                                                                             H       H     "                                                       "        CH.sub.3                                                                               H     "                                                        ##STR302##                                                                             H       H     "                                                       "        CH.sub.3                                                                               H     "                                                        ##STR303##                                                                     ##STR304##                                                                     ##STR305##                                                                     ##STR306##                                                                     ##STR307##                                                                     ##STR308##                                                                     ##STR309##                                                                     ##STR310##                                                                     ##STR311##                                                                     ##STR312##                                                                     ##STR313##                                                                    ______________________________________                                         OH                                                                             CH.sub.3                                                                        ##STR314##                                                                     ##STR315##                                                                     ##STR316##                                                                     ##STR317##                                                                     ##STR318##                                                                     ##STR319##                                                                     ##STR320##                                                                     ##STR321##                                                                    R    R.sup.1                                                                               R.sup.2                                                                              R.sup.3                                                                              R.sup.4                                                ______________________________________                                         H    F.sub.3 C                                                                             H     C.sub.2 H.sub.5                                                                      C.sub.4 H.sub.9 n                                      H    F.sub.3 C                                                                             H     nC.sub.3 H.sub.7                                                                      ##STR322##                                            H.sub.3 C                                                                           H.sub.3 C                                                                             H     H                                                                                     ##STR323##                                            H    F.sub.3 C                                                                             NH.sub.2                                                                             nC.sub.3 H.sub.7                                                                     nC.sub.3 H.sub.7                                        ##STR324##                                                                     ##STR325##                                                                     ##STR326##                                                                     ##STR327##                                                                     ##STR328##                                                                     ##STR329##                                                                     ##STR330##                                                                     ##STR331##                                                                     ##STR332##                                                                     ##STR333##                                                                     ##STR334##                                                                     ##STR335##                                                                     ##STR336##                                                                    R            R.sup.1       R.sup.2                                             ______________________________________                                         CH.sub.3     CH.sub.3      CH(C.sub.6 H.sub.3).sub.2                            ##STR337##  H             C.sub.2 H.sub.5                                      ##STR338##  iC.sub.3 H.sub.7                                                                             CH.sub.2 Cl                                          ##STR339##  CH.sub.2OC.sub.2 H.sub.5                                                                     CH.sub.2 Cl                                          ##STR340##  CH.sub.2CH.sub.2OCH.sub.3                                                                    CH.sub.2 Cl                                         CH.sub.2CHCH.sub.2                                                                          CH.sub.2CHCH.sub.2                                                                           CH.sub.2 Cl                                         ______________________________________                                    

In many instances it may be advantageous to combine or mix the compounds according to the invention with other growth-regulating active ingredients, e.g., compounds of various chemical structure which form ethylene (e.g., phosphonic acid derivatives and silanes, ethyl hydrazines), and onium compounds (e.g., trimethylammonium, hydrazonium and sulfonium salts, and derivatives of morpholinium, piperidinium and pyridazinium compounds). Also of interest are other growth-regulating substances, for instance from the group of trifluoromethylsulfonamido-p-acetotoluidides, maleic hydrazide, abscisic acid derivatives, chlorinated phenoxy fatty acids having an auxinic action, and polyhydric alcohols and fatty acid esters having a specific action on meristematic tissue areas.

The amount used of the agents according to the invention may vary, and depends in the main on the type of effect desired.

The application rate is generally from 0.1 to 15 and more, preferably from 0.2 to 6, kg of active ingredient per hectare.

The agents according to the invention influence the growth of plant parts above and in the soil in a different manner; employed in the usual concentrations, they have a low toxicity to warm bloods.

The new agents have an effect on the physiology of plant growth and may be used for various purposes. The different effects of these active ingredients depend in essence on the time of application, based on the development stage of the seed or plant, and on the concentrations employed.

The influence on vegetative development is manifested in particular in a reduction in growth height, giving numerous plants, especially cereals, increased rigor and reducing the tendency toward lodging. Simultaneously, tillering is improved, resulting in an increase in ear-bearing stems per unit area.

In grass, the reduced growth height gives a denser, more resistant sward, this in particular enabling the mowing frequency to be reduced. This is a considerable labor-saving advantage for lawns, grass verges and in parks. The reduction in growth height is also accompanied by an increase in the chlorophyll content, as a result of which grass and other plants take on a much deeper green.

The influence on vegetative growth also considerably increases flowering and fruiting in numerous plants, e.g., cotton and soybeans.

Of particular importance is the surprising phenomenon that treatment with the substances according to the invention induces rooting. This results in a more rational use of water and nutrients by the treated plants, thus increasing their resistance not only to dryness but also to cold (frost).

The possibilities of using the compounds of the invention in fruit and ornamentals, in landscaping (including appropriate influence of the vegetation on barren land), and airfields and training compounds are varied and extensive.

The substances may also be successfully used for hastening ripening and flowering, and in special methods of cultivation.

The new agents may also positively influence the concentration of important plant constituents such as sugar and proteins.

The extent and degree of action depend on various factors, especially the time of application in relation to the development stage of the plant and the concentration employed. These factors are, in turn, different for different plant species and depend on the effect desired. For instance, lawns will be treated during the whole growth period; ornamentals in which it is desired to increase the bloom intensity and number of buds, before budding; and plants whose fruit is to be used or processed, an appropriate length of time before the harvest. Various derivatives of the class of compounds described here have herbicidal properties, and are therefore suitable for removing and controlling unwanted plants.

EXAMPLES 7-10

Action on wheat, barley and oats

In the greenhouse, the four cereals wheat ("Opal" variety), rye ("Petkuser"), barley ("Villa") and oats ("Flamingskrone") were sown in plastic dishes 11.5 cm in diameter in a sandy loam adequately supplied with nutrients. The active ingredients were applied at various rates to the soil and to the leaves. When applied to the soil, the active ingredient were sprayed onto the surface of the soil on the day of sowing; in the case of leaf treatment, the leaves were sprayed in the usual manner at a growth height of the plants of 10 cm. During the 18 day growth period, the treated plants grew much more slowly than the untreated control, a fact later confirmed by measurements of the stem length. Measurements were taken of 100 plants from each series. As a result of the use of transparent plastic dishes it was surprisingly ascertained that root growth had been promoted in the treated series.

The prior art agent used for comparison purposes was N-2-chloroethyl-N,N,N-trimethylammonium chloride (CCC; German Printed Application DAS No. 1,294,734).

The results are given in the following tables.

EXAMPLE 7

    ______________________________________                                         Influence on the growth height of wheat (soil and leaf                         treatment)                                                                                   Applica-                                                                       tion                                                                           rate     Plant height                                            Active ingredient                                                                              kg/ha     in cm     relative                                   ______________________________________                                         (A) Soil treatment                                                             Control         --        31.0      100                                        CCC             0.5       26.0      83.9                                                       1.0       24.5      79.0                                                       2.0       22.5      72.6                                                       6.0       22.0      71.0                                        ##STR341##     0.5 1.0 2.0 6.0                                                                          28.5 23.0 20.5 10.5                                                                      91.9 74.2 66.1 33.9                         ##STR342##     0.5 1.0 2.0 6.0                                                                          27.5 22.5 88.7 72.6 50.0 31.7                        (B) Leaf treatment                                                             Control         --        30.0      100                                        CCC             0.125     28.0      93.3                                                       0.5       26.0      86.7                                                       1.0       26.0      86.7                                                       2.0       23.0      76.7                                                       4.0       23.0      76.7                                        ##STR343##     0.125 0.5 1.0 2.0 4.0                                                                    24.0 22.0 20.0 19.0 17.5                                                                 80.0 73.3 66.6 63.3 58.3                    ##STR344##     0.125 0.5 1.0 2.0 4.0                                                                    25.0 23.5 21.0 21.5 20.0                                                                 83.3 78.3 70.0 71.7 66.7                   ______________________________________                                    

EXAMPLE 8

    ______________________________________                                         Influence on the growth height of rye (soil and leaf treatment)                                Application                                                                    rate   Plant height                                            Active ingredient kg/ha    in cm    relative                                   ______________________________________                                         (A) Soil treatment                                                             Control           --       29.0     100                                        CCC               0.5      28.0     96.6                                                         1.0      27.5     94.8                                                         2.0      28.0     96.6                                                         6.0      26.5     91.4                                        ##STR345##       0.5 1.0 2.0 6.0                                                                         22.5 19.0 13.0  8.5                                                                     77.6 65.5 44.8 29.3                         ##STR346##       0.5 1.0 2.0 6.0                                                                         23.0 22.5 19.0  9.0                                                                       79.3 77.6 65.5 31.0                      (B) Leaf treatment                                                             Control           --       29.5     100                                        CCC               0.125    29.0     98.3                                                         0.5      28.0     94.9                                                         1.0      27.5     93.2                                                         2.0      27.5     93.2                                                         4.0      29.0     98.3                                        ##STR347##       0.125 0.5 1.0 2.0 4.0                                                                   24.5 20.0 18.5 17.5 16.0                                                                83.1 67.8 62.7 59.3 54.2                    ##STR348##       0.125 0.5 1.0 2.0 4.0                                                                   25.0 20.5 22.0 18.0 18.5                                                                84.7 69.5 74.6 61.0 62.7                   ______________________________________                                    

EXAMPLE 9

    ______________________________________                                         Influence on the growth height of barley (soil and leaf treatment)                            Application                                                                    rate    Plant height                                            Active ingredient                                                                               kg/ha     in cm    relative                                   ______________________________________                                         (A) Soil treatment                                                             Control          --        31.5     100                                        CCC              0.5       28.0     88.9                                                        1.0       27.0     85.7                                                        2.0       26.0     82.5                                                        6.0       25.0     79.4                                        ##STR349##      0.5 1.0 2.0 6.0                                                                          28.0 28.0 23.5 16.5                                                                     88.9 88.9 74.6 52.4                         ##STR350##      0.5 1.0 2.0 6.0                                                                          30.5 29.0 24.5 19.0                                                                     96.8  92.1 77.8 60.3                       (B) Leaf treatment                                                             Control          --        30.0     100                                        CCC              0.125     29.0     96.7                                                        0.5       28.5     95.0                                                        1.0       26.5     88.3                                                        2.0       27.0     90.0                                                        4.0       27.0     90.0                                        ##STR351##      0.125 0.5 1.0 2.0 4.0                                                                    24.0 23.0 21.5 20.5 18.5                                                                80.0 76.7 71.7 68.3 61.7                    ##STR352##      0.125 0.5 1.0 2.0 4.0                                                                    25.5 23.5 22.0 20.5 20.0                                                                85.0 78.3 73.3 68.3 66.7                   ______________________________________                                    

EXAMPLE 10

    ______________________________________                                         Influence on the growth height of oats (soil and leaf treatment)                             Application                                                                    rate     Plant height                                            Active ingredient                                                                              kg/ha      in cm    relative                                   ______________________________________                                         (A) Soil treatment                                                             Control         --         28.0     100                                        CCC             0.5        28.0     100                                                        1.0        28.0     100                                                        2.0        27.0     96.4                                                       6.0        26.0     92.9                                        ##STR353##     0.5 1.0 2.0 6.0                                                                           25.0 24.0 21.0 15.0                                                                     89.3 85.7 75.0 53.6                         ##STR354##     0.5 1.0 2.0 6.0                                                                           28.0 26.5 24.5 15.5                                                                     100  94.6 87.5 55.4                        (B) Leaf treatment                                                             Control         --         28.0     100                                        CCC             0.125      28.0     100                                                        0.5        28.5     101.8                                                      1.0        28.0     100                                                        2.0        27.0     96.4                                                       4.0        25.5     91.1                                        ##STR355##      0.125 0.5 1.0 2.0 4.0                                                                    23.5 22.5 21.0 19.0 17.0                                                                83.9 80.4 75.0 67.9 60.7                    ##STR356##      0.125 0.5 1.0 2.0 4.0                                                                    25.5 25.0 22.5 22.5  22.0                                                               91.1 89.3 80.4 80.4 78.6                   ______________________________________                                    

EXAMPLE 11

Influence on stem length of cereals and Gramineae

The compounds listed in the following Tables A and B were examined by the method described below as to their effect on the crop plants listed in these tables:

The vessels used for the experiments were plastic pots having a volume of 1,130 cm³ (Table A) or paraffined paper cups having a volume of 170 cm³ (Table B). The pots and cups were filled with a sandy loam. The seeds of the test plants--separated by species--were sown shallow. Preemergence treatment (soil treatment) was effected immediately after sowing and before germination of the seeds. Seeds lying on the surface came into contact with the active ingredients. Postemergence treatment (leaf treatment) took place at an average growth height of the plants (depending on the rate of growth) of from 6 to 10 cm. The substances were suspended, emulsified or dissolved in water as diluent and applied by means of fine nozzles. The vessels were kept in a greenhouse in a temperature range of 12° C. to 25° C., and were regularly sprinkler irrigated for the duration of the experiment. The observation period was 6 to 8 weeks.

Results

Tables (A) and (B) contain compounds which exercise a strong influence on the development of the plant shoots. This growth inhibition of the parts of the plant above ground is desirable, and is not accompanied by disadvantageous symptoms such as chlorosis. The treated plants were usually conspicous for their dark green leaves.

EXAMPLE 11

                                      TABLE (A)                                    __________________________________________________________________________     Influence on the growth height of young cereal plants                                                    Growth height in cm after                                                      soil treatment                                                                         leaf treatment                                                Application rate                                                                        Triticum                                                                               Hordeum                                                                             Triticum                                Active ingredient                                                                               kg/ha    aestivum                                                                               vulgare                                                                             aestivum                                __________________________________________________________________________     Control          --       42      37   44                                      [ClCH.sub.2CH.sub.2N(.sup.⊕CH.sub.3).sub.3 ] .sup.⊖Cl                               0.5      40      36   40                                                       1.0      40      31   40                                      CCC (prior art)  2.0      33      33   40                                       ##STR357##      0.5 1.0 2.0                                                                             16 15  0                                                                               40 39 38                                                                            42 27 20                                 ##STR358##      0.5 1.0 2.0                                                                             25 25 20                                                                               40 38 33                                                                            40 34 35                                 ##STR359##      0.5 1.0 2.0                                                                             40 40 30                                                                               48 44 41                                                                            40 39 40                                 ##STR360##       0.25 0.5 1.0 2.0                                                                       26 15 -- --                                                                            -- 43  40 30                                                                        29 25 13 12                              ##STR361##      0.5 1.0 2.0                                                                             22 12 10                                                                               40 42 31                                                                            35 33 33                                 ##STR362##      0.5 1.0 2.0                                                                             24 20 16                                                                               38 30 27                                                                            33 28 17                                 ##STR363##      0.5 1.0 2.0                                                                             26 26 13                                                                               36 36 29                                                                            28 28 17                                 ##STR364##       0.25 0.5 1.0 2.0                                                                       32 28 20 23                                                                            -- 36 39 31                                                                         30 23 26 20                              ##STR365##       0.25 0.5 1.0 2.0                                                                       22 12  6  7                                                                            36 30 18 14                                                                         36 30 28 25                             __________________________________________________________________________

EXAMPLE 11

                                      TABLE (B)                                    __________________________________________________________________________     Influence on the growth height of Gramineae (soil and leaf treatment)                                      % growth inhibition compared with untreated                                    control after                                                                  soil treatment                                                                              leaf treatment                                            Application rate                                                                       Avena                                                                              Hordeum                                                                             Lolium                                                                             Avena                                                                              Hordeum                                                                             Lolium                       Active ingredient   kg/ha   sativa                                                                             vulgare                                                                             multifl.                                                                           sativa                                                                             vulgare                                                                             multifl.                     __________________________________________________________________________      ##STR366##         3.0     25  10   5   45  10   20                           CCC (bekannt)                                                                   ##STR367##         3.0     30  30   30  50  50   30                            ##STR368##         3.0     20   0    0  40  35   20                            ##STR369##         3.0     30  40     30.sup.+                                                                         40  30   25                            ##STR370##         3.0     60  35   --  20  20    0                            ##STR371##         3.0     60  60   50  60  50   50                            ##STR372##         3.0     40    60.sup.+                                                                          50  50  50   50                           __________________________________________________________________________      0 = no inhibition                                                              100 = no growth                                                                .sup.+  = leaf necroses due to too high phytotoxicity                    

EXAMPLE 12

Action on stem length, number of lateral shoots and yield in spring barley

To examine the effect of the various substances on spring barley up to the maturity stage of the plants, an experiment was carried out in large pots. The plants were grown in quartz sand (fertilized with 2 g N as ammonium nitrate in 3 doses, 1 g P₂ O₅ as secondary sodium phosphate, 1.5 g K₂ O as potassium sulfate, 0.5 g MgO as magnesium sulfate, 10 ml of a solution of trace elements, and 10 mg of iron as an iron complex). The active ingredients were applied to the leaves twice, once at a rate of 0.5 kg/ha and once at a rate of 1.5 kg/ha, at a plant height of 35 to 40 cm. The treated plants were up to 10% shorter than the control, and yields were also slightly up. The results of this experiment are given below.

EXAMPLE 13

Action on grass or lawns

Lawn seed of the standard mixture Agrostis tenius (10%) Cynosurus cristatus (10%), Festuca rubra (15%), Lolium perenne (35%) and Poa praetensis (30%) was sown in a loam in large pots. The soil was fertilized with 1.5 g N as ammonium nitrate and 1 g P₂ O₅ as secondary potassium phosphate. After the grass had been cut twice, it was sprayed in conventional manner at a height of 4 cm with the active ingredients at various application rates. 19 days after treatment the growth height and dry substance content were determined. The treated grass was much shorter than the control, and produced a correspondingly lower amount of dry substance.

It was also observed that as the amount of compound according to the invention increased the color of the grass turned an intensive deep green. The results of this experiment are given below. The prior art compound used for comparison purposes was maleic hydrazide (M; German 815,192).

EXAMPLE 12

    __________________________________________________________________________     Influence on stem length, number of lateral shoots and yield in spring         barley                                                                                           Stem length                                                                            No. of lateral shoots                                                                    Ear weight                                 Active ingredient cm relative                                                                            no.  relative                                                                            g  relative                                __________________________________________________________________________     Control           76.9                                                                              100  93   100  90.4                                                                              100                                     CCC            3 kg/ha                                                                           74.2                                                                              96.5 99   106.5                                                                               95.0                                                                              105.1                                    ##STR373##  0.5 kg/ha 1.5 kg/ha                                                                 74.1 69.7                                                                         96.4 90.6                                                                           105 111                                                                             112.9 119.4                                                                         91.5 94.8                                                                         101.2 104.9                             __________________________________________________________________________

EXAMPLE 13

    __________________________________________________________________________     Action of grass or lawns                                                                                   19 days after                                                    Application                                                                          First cutting,                                                                         treatment             First cutting,                                                                 chlorophyll                                rate  growth height                                                                          dry substance                                                                          Observations  content                      Active ingredient                                                                            kg/ha cm relative                                                                            g  relative                                                                            (color)       g Ca + b/100 g               __________________________________________________________________________                                                       TS                           Control       --    25.5                                                                              100  12.5                                                                              100  normal green  1.33                         M             0.25  25.0                                                                              98.0 10.5                                                                              84.0 normal green  --                                         0.5   24.5                                                                              96.0 10.5                                                                              84.0 normal green  --                                         1.0   20.0                                                                              78.4 7.3                                                                               58.4 normal green  --                                         2.0   16.0                                                                              62.7 6.0                                                                               48.0 lighter green                                                                           reddish                                                                             1.11                                       4.0   12.5                                                                              49.0 4.5                                                                               36.0 lighter green                                                                           brown in                                                                            --                                                                        places                             ##STR374##   0.25  0.5 1.0 2.0 4.0                                                                26.0 24.0 19.0 16.0 10.5                                                          101.9 94.1 74.5 62.7 41.1                                                           10.7 8.6 7.0 4.8 3.1                                                              85.6 68.8 56.0 38.4 24.8                                                            normal green normal green normal                                               green dark green dark                                                                        -- -- -- -- --                ##STR375##   0.25 0.5 1.0 2.0 4.0                                                                 25.0 24.0 21.5 18.0 12.5                                                          98.0 94.1 84.2 70.5 49.0                                                            12.8 11.4 8.4 6.3 4.1                                                             102.4 91.2 67.2 50.4 32.8                                                           normal green normal green normal                                               green dark green dark                                                                        -- -- --  1.40 --            __________________________________________________________________________

EXAMPLE 14

Long-term action on lawns

A further experiment was carried out on lawns under the same conditions as in Example 13. To investigate the long-term action of the compounds of the invention, the growth of the grass was observed for 3 cuttings after treatment, and in the period of renewed growth after each cutting the shortening effect and the corresponding decrease in dry substance were ascertained. The good long-term action of the agents examined is apparent from the following table. The prior art compound used for comparison purposes was the diethanolamine salt of 3-trifluoromethylsulfonamido-p-acetotoluidide (S; Proc. Northeast. Weed Sci. Soc., 29, 403-408, 1975).

EXAMPLE 14

    __________________________________________________________________________     Long-term action on lawns                                                                           First cutting   Second cutting                                           Application      green            green                                                                                Third cutting           Active         rate  growth height                                                                             weight                                                                              growth height                                                                              weight                                                                              green weight             ingredient     kg/ha cm relative                                                                            g  relative                                                                            cm  relative                                                                            g  relative                                                                            g   relative             __________________________________________________________________________     Control        --    18.0                                                                              100  35.3                                                                              100  14,7                                                                               100  26,7                                                                              100  15,2                                                                               100                  S              0.5   14.5                                                                              80.6 26.7                                                                              75.6 14.0                                                                               95.2 27.3                                                                              102.2                                                                               15.6                                                                               102.6                               1.0   13.0                                                                              72.2 23.0                                                                              65.2 12.5                                                                               85.0 27.6                                                                              103.4                                                                               15.0                                                                               98.6                                2.0   10.5                                                                              58.3 12.6                                                                              35.7 9.5 64.6 20.1                                                                              75.3 13.7                                                                               90.1                                4.0   9.0                                                                               50.0 9.4                                                                               26.6 4.5 30.6 9.6                                                                               36.0 10.4                                                                               68.4                  ##STR376##    0.5 1.0 2.0 4.0                                                                       14.5 12.5 11.0 10.5                                                              80.6 69.5 61.1 58.3                                                                 25.5 24.4 22.0 16.5                                                               72.2 69.1 62.3 46.7                                                                 14.5 11.5 8.0 7.0                                                                  98.6 78.2 54.5 47.6                                                                 27.8 25.1 18.7 13.2                                                               104.1 94.0 70.0 49.4                                                                16.5 16.5 14.0                                                                     108.6 108.6                                                                    92.1 67.8             ##STR377##    0.5 1.0 2.0 4.0                                                                      16.5 13.5 11.5 9.0                                                                91.7 75.0 63.9 50.0                                                                 28.8 21.3 17.2 13.9                                                               81.6 60.3 48.7 39.4                                                                 12.5 9.0 7.5 5.0                                                                   85.0 61.2 51.0 34.0                                                                 27.2 20.5 16.2 10.2                                                               101.9 76.8 60.7 38.2                                                                17.2 15.1 12.5                                                                     113.2 99.3 82.2                                                                4.5                   ##STR378##    0.5 1.0 2.0 4.0                                                                      18.5 16.5 14.5 12.5                                                               102.8 91.7 80.6 69.5                                                                31.8 27.1 20.3 19.5                                                               90.1 76.8 57.5 55.2                                                                 14.0 13.0 9.0 7.0                                                                  95.2 88.4 61.2 47.6                                                                 28.8 25.8 19.1 16.8                                                               107.9 96.6 71.5 62.9                                                                15.5 15.3 12.8                                                                     102.0 100.7                                                                    84.2 84.2             ##STR379##    0.5 1.0 2.0  4.0                                                                     15.0 12.5 7.5 6.5                                                                 83.3 69.5 41.7 36.1                                                                 23.1 20.5 9.8 7.9                                                                 65.4 58.1 27.8 22.4                                                                 10.0 9.0 5.0 2.0                                                                   68.0 61.2 34.0 13.6                                                                 21.8 21.4 10.1 7.1                                                                81.6 80.1 37.8 26.6                                                                 14.6 13.5 9.5                                                                      96.1 88.8 62.5                                                                 52.0                  ##STR380##    0.5 1.0 2.0 4.0                                                                      14.0 14.0 12.5 9.5                                                                77.8 77.8 69.5 52.8                                                                 26.8 25.5 20.0 13.2                                                               75.9 72.2 56.7 37.4                                                                 13.0 12.5 22.0 7.5                                                                 88.4 85.0 74.8 51.0                                                                 23.5 22.0 21.4 15.3                                                               88.0 82.4 80.1  57.3                                                                16.5 16.3 15.7                                                                     108.6 107.2                                                                    103.3 91.4           __________________________________________________________________________

EXAMPLE 15

Action on individual grasses

Under the same conditions as in Example 13 the two grasses Festuca rubra and Poa praetensis (both components of the lawn mixture used in Example 13) were grown in a neutral sandy loam. The growth height was measured 3 weeks after treatment with the active ingredients. The results given below demonstrate the shortening effect of the compounds of the invention; Poa praetensis is influenced more strongly than Festuca rubra.

EXAMPLE 15

    ______________________________________                                         Influence on the growth height of the grasses                                  Festuca rubra and Poa praetensis                                                            Appli-                                                                               Festuca rubra                                                                             Poa praetensis                                                cation                                                                               growth height                                                                             growth height                                                   rate            rela-      rela-                                Active ingredient                                                                             kg/ha   cm      tive cm    tive                                 ______________________________________                                         Control        --      27.5    100  22.5  100                                  M              0.5     28.0    101.8                                                                               23.0  102.2                                               1.0     28.5    103.6                                                                               22.0  97.8                                                2.0     26.5    96.4 22.0  97.8                                  ##STR381##    0.5 1.0 2.0                                                                            27.0 25.5 23.5                                                                         98.2 92.7 85.5                                                                      20.0 20.0.sup.+ 15.5.sup.+                                                           88.9 88.9 68.9                        ##STR382##    0.5 1.0 2.0                                                                            29.5 27.5 25.5                                                                         107.3 100.0 92.7                                                                    19.0 17.5.sup.+ 14.0.sup.+                                                           84.4 77.8 62.2                       ______________________________________                                          .sup.+ plants a darker green                                             

EXAMPLE 16

Action of soybeans (hydroponic treatment)

Young soybean plants grown in quartz sand were transferred to hydroponic treatment in 4 liter vessels and provided with a sufficient supply of nutrient solution and trace elements. The active ingredients were added (0.25 mg/vessel=0.06 ppm; 1.0 mg/vessel=0.25 ppm; 2.5 mg/vessel=0.63 ppm) at a plant height of approx. 22 cm. The plants were in continuous contact with the active ingredients. During the growth period of 4 weeks the growth height of the treated plants was considerably reduced, compared with the control. The roots were also shorter, but the plants had more and stronger shoots. The results are given below.

EXAMPLE 16

    __________________________________________________________________________     Influence on the growth of roots and shoots of soybeans (hydroponic            treatment)                                                                                  Application                                                                          Shoot        Root                                                        rate  length                                                                               dry substance                                                                         length                                                                               dry substance                            Active ingredient                                                                           ppm   cm rel.                                                                              g   rel.                                                                              cm rel.                                                                              g   rel.                                 __________________________________________________________________________     Control      --    74.3                                                                              100                                                                               41.1                                                                               100                                                                               30.3                                                                              100                                                                               13.3                                                                               100                                   ##STR383##  0.06 0.25 0.63                                                                       70.7 62.3 51.7                                                                    95.4 84.1 69.8                                                                    39.0 31.5 26.6                                                                     94.9 76.6 64.7                                                                    28.3 24.7 24.7                                                                    93.4 81.5 81.5                                                                    13.5 13.2 15.0                                                                     97.1 95.0 107.9                      __________________________________________________________________________

EXAMPLE 17 a-c

Action on soybeans, field beans and sunflowers

The action on soybeans, field beans and sunflowers was examined under the same conditions as in Example 16. The shoots and roots of all 3 crop plants were considerably shortened. Whereas in the shoots the dry substance was reduced commensurately with the shortening, the dry substance in the roots rose (particularly in soybeans) as the concentration increased. The results are given below.

EXAMPLE 17 a

    __________________________________________________________________________     Action on soybeans (hydroponic treatment)                                                   Application                                                                          Shoot        Root                                                        rate  length                                                                               dry substance                                                                         length                                                                               dry substance                            Active ingredient                                                                           ppm   cm rel.                                                                              g   rel.                                                                              cm rel.                                                                              g   rel.                                 __________________________________________________________________________     Control      --    36.7                                                                              100                                                                               5.8 100                                                                               28.7                                                                              100                                                                               1.1 100                                   ##STR384##  0.06 0.25 0.63                                                                       33.0 21.7 19.0                                                                    89.9 59.1 51.8                                                                    5.4 4.9 3.9                                                                        93.1 84.5 67.2                                                                    21.7 20.0 20.0                                                                    75.6 69.7 69.7                                                                    1.5 1.5 2.1                                                                        136.4 136.4 190.9                    __________________________________________________________________________

EXAMPLE 17 b

    __________________________________________________________________________     Action of field beans (hydroponic treatment)                                                Application                                                                          Shoot        Root                                                        rate  length                                                                               dry substance                                                                         length                                                                               dry substance                            Active ingredient                                                                           ppm   cm rel.                                                                              g   rel.                                                                              cm rel.                                                                              g   rel.                                 __________________________________________________________________________     Control      --    73.0                                                                              100                                                                               16.9                                                                               100                                                                               41.3                                                                              100                                                                               6.2 100                                   ##STR385##  0.06 0.25 0.63                                                                       69.7 67.3 56.7                                                                    95.5 92.2 77.7                                                                    14.5 14.5 13.0                                                                     85.8 85.8 76.9                                                                    28.3 28.3 25.0                                                                    68.5 68.5 60.5                                                                    3.8 5.3 6.0                                                                        63.3 85.5 96.8                       __________________________________________________________________________

EXAMPLE 17 c

    __________________________________________________________________________     Action on sunflowers (hydroponic treatment)                                                 Application                                                                          Shoot        Root                                                        rate  length                                                                               dry substance                                                                         length                                                                               dry substance                            Active ingredient                                                                           ppm   cm rel.                                                                              g   rel.                                                                              cm rel.                                                                              g   rel.                                 __________________________________________________________________________     Control      --    41.3                                                                              100                                                                               6.4 100                                                                               20.0                                                                              100                                                                               1.5 100                                   ##STR386##  0.06 0.25 0.63                                                                       35.0 27.3 27.3                                                                    84.7 66.1 66.1                                                                    6.3 5.3 5.2                                                                        98.4 82.8 81.3                                                                    18.7 16.7 12.7                                                                    93.5 83.5 63.5                                                                    1.5 1.4 1.6                                                                        100 93.3 106.7                       __________________________________________________________________________

EXAMPLE 18

Action on cotton

Cotton plants were subjected to hydroponic treatment under the same conditions as in Example 16. The active ingredients were added (1.25 mg/vessel=0.3 ppm and 5 mg/vessel=1.25 ppm) at a height of the plants of 15 to 18 cm. During the 4 week growth period it was not only observed that the treated plants were considerably shortened, but also that the buds of the control plants and those treated with CCC withered in the nascent stage and dropped off, whereas the other treated plants developed a surprisingly large number of distinct squares. The results below are averages from 3 vessels, each of 3 plants.

EXAMPLE 18

    ______________________________________                                         Induction of flowering and influence on the growth height                      of cotton (hydroponic treatment)                                                            Appli-           No.                                                           cation           of squares                                                    rate  Shoot length                                                                              per vessel                                       Active ingredient                                                                             ppm     cm      rel. (3 plants)                                 ______________________________________                                         Control        --      47.2    100  0                                          CCC            0.3     36.2    76.7 0                                                         1.25    34.8    73.8 0                                           ##STR387##    0.3 1.25                                                                               40.2 27.8                                                                              85.2 58.9                                                                           4.0 8.7                                     ##STR388##    0.3 1.25                                                                               41.9 30.9                                                                              88.8 65.5                                                                           2.6 8.3                                    ______________________________________                                    

EXAMPLE 19

Action on soybeans in a vegetation experiment in sandy soil

Soybean plants of the Gieso variety were grown in a neutral sandy loam. Fertilization took place at the time of sowing, with 0.5 g N as ammonium nitrate and 1.0 g P₂ O₅ as secondary potassium phosphate. The active ingredients were applied to the soil at rates of 3 and 6 kg/ha at a growth height of the plants of 10 to 12 cm.

After 4 weeks, the treated plants were much shorter than the control, and looked more compact as a result of the different angle of the leaves. The results are given below. The prior art compound used for comparison purposes was 2,3,5-triiodobenzoic acid (T; U.S. Pat. No. 2,978,838).

EXAMPLE 19

    ______________________________________                                         Action on soybeans in a vegetation experiment in a sandy loam                                Application rate                                                                         Growth height                                          Active ingredient                                                                              kg/ha       cm      relative                                   ______________________________________                                         Control         --          23.0    100                                        T               0.125       23.5    102.2                                                      0.375       25.0    108.7                                                      0.750       23.0    100.0                                       ##STR389##     3.0 6.0     15.0 14.0                                                                              65.2 60.9                                   ##STR390##     3.0 6.0     17.5 14.5                                                                              76.1 63.0                                   ##STR391##     3.0 6.0     13.5 12.5                                                                              58.7 54.4                                   ##STR392##     3.0 6.0     17.5 13.5                                                                              76.1 58.7                                   ##STR393##     3.0 6.0     14.0 14.0                                                                              60.9 60.9                                   ##STR394##     3.0 6.0     21.0 17.0                                                                              91.3 73.9                                   ##STR395##     3.0 6.0     17.0 16.0                                                                              73.9 69.6                                  ______________________________________                                    

EXAMPLE 20

Action on sugar beet

Sugar beets of the KAWpoly variety were grown in a neutral sandy loam in large pots. Fertilization with 1.5 g N as ammonium nitrate and 1 g P₂ O₅ as secondary potassium phosphate took place at the time of sowing. At a plant height of 16 to 18 cm the leaves were treated twice, once with 0.5 kg/ha and once with 1 kg/ha; in each case, 4 pots formed a variation of the experiment. After harvesting, the yield and sugar content in the beets and the lower stems were found to have been improved by the treatment. The results are given in the following table.

EXAMPLE 20

    __________________________________________________________________________     Influence on yield and sugar content of sugar beet                                                                     Sugar content of                                     Application                                                                          Yield      Sugar content                                                                           lower stems                                          rate  g dry sub- % in dry % in dry                               Active ingredient                                                                            kg/ha stance/vessel                                                                         rel.                                                                               substance                                                                           rel.                                                                               substance                                                                           rel.                              __________________________________________________________________________     Content       --    12.4   100 50.3 100 22.7 100                                ##STR396##   0.5 1.0                                                                              13.04 14.39                                                                           107.4 118.5                                                                        51.0 52.2                                                                           101.4 103.8                                                                        22.9 25.8                                                                           100.9 113.6                       __________________________________________________________________________

EXAMPLE 21

Influence on the sugar content of sugar beet in the open

The active ingredient was applied to small plots in an ordinary beet field to demonstrate the positive influence on sugar production under field conditions. The crop plant was Beta vulgaris sap. altissima, variety "Kleinwanzleben KAWPoly". The soil was a sandy loam (1.5% organic substance, pH 5.7). Mineral fertilization totalled 400 kg N, 100 kg P₂ O₅, and 100 kg K₂ O per hectare. For chemical weed control, 2.5 kg/ha of 1-phenyl-4-amino-5-chloropyridazone-(6) was applied before emergence of the beet plants. Aphids were controlled with dimethoate (O,O-dimethyl-S-(N-methylcarbonylmethyl)-phosphorus dithioate). Sowing took place on Mar. 10, 1975. The beets were lifted comparatively early on Sept. 29, 1975. The active ingredient was applied with the aid of spraying equipment with fine nozzles, mounted on a tractor. The amount of water used for dispersion purposes was 780 liters/ha. Treatment was effected on 2 different dates and on different plots:

I the beet had 5 to 7 true leaves;

II five weeks before harvesting, on the well developed plants. The sugar content was determined from fresh beets immediately after lifting.

The following results may be recorded:

(1) There was no impairment of the beets during the growth period.

(2) The sugar yields overall were low as a result of the early lifting. However, the sugar content was significantly improved by the active ingredient (cf. table).

The results with sugar beet are an indication of the increased production of desirable plant constituents as a consequence of treatment with a representative of the class of compounds described.

EXAMPLE 21

    ______________________________________                                         Increase in the                                                                sugar content of sugar beet by chemical treatment in the open                                                         freshly                                                                 Sugar  lifted                                                  Appli-          content                                                                               beet                                                    cation          in     rela-                                                   rate    Date    absolute                                                                              tive in-                                Active ingredient                                                                              kg/ha   treated %      crease                                  ______________________________________                                         Control         --      --      12.6 a.sup.++                                                                         100                                      ##STR397##     2.0 2.0 I.sup.+ II                                                                             14.35 b 13.85 ab                                                                      113 110                                 ______________________________________                                          .sup.+ I = 20.05.75 Harvest: 29.09.75                                          II = 21.08.75                                                                  .sup.++ Values which have letters in common are not significantly              different (Duncan's new multiple range test, level 0.05%).               

EXAMPLE 22

Action on tomatoes

Tomatoes were grown in the greenhouse in glass dishes 11.5 cm in diameter containing a peat substrate which was provided with an adequate supply of nutrients. The active ingredients were sprayed onto the leaves in conventional manner at a plant height of 9 to 12 cm. After 14 days the treated plants were shorter than the control, and had a deeper color.

    ______________________________________                                                      Application rate                                                                           Plant height                                          Active ingredient kg/ha      cm     relative                                   ______________________________________                                         Control           --         27.2   100                                         ##STR398##       1.5 3.0 6.0                                                                               24.3 20.3 14.0                                                                        89.3 74.6 51.5                              ##STR399##       1.5 3.0 6.0                                                                               25.0 22.7 15.3                                                                        91.9 83.5 56.2                             ______________________________________                                    

EXAMPLE 23

Action on rice

Rice was grown in the greenhouse under the same conditions as in Example 22. At a growth height of 11 to 13 cm the active ingredients were sprayed onto the leaves in the usual manner. The plants were measured after 66 days. The treated plants were up to 30% shorter than the control.

    ______________________________________                                                      Application rate                                                                           Plant height                                          Active ingredient kg/ha      cm     relative                                   ______________________________________                                         Control           --         40.6   100                                        CCC               1.0        38.0   93.6                                                         2.0        40.5   99.8                                                         4.0        38.5   94.8                                                         6.0        40.0   98.5                                        ##STR400##       1.0 2.0 4.0 6.0                                                                           35.0 33.0 29.5 28.5                                                                   86.2 81.3 72.7 70.2                         ##STR401##       1.0 2.0 4.0 6.0                                                                           37.0 37.0 34.5 33.5                                                                   91.1 91.1 85.0 82.5                        ______________________________________                                    

EXAMPLE 24

Action on sunflowers

Sunflowers were grown under the same conditions as in Example 22. The active ingredients were applied both to the soil and to the leaves. Both methods of treatment resulted in much shorter plants than the control.

    ______________________________________                                                      Application rate                                                                           Plant height                                          Active ingredient kg/ha      cm     relative                                   ______________________________________                                         (A) Soil treatment                                                             Control           --         36.3   100                                        CCC               3.0        40.0   110                                                          12.0       36.0   99                                          ##STR402##       3.0 12.0   26.5 15.5                                                                             73 43                                       ##STR403##       3.0 12.0   30.5 22.5                                                                             84 62                                      (B) Leaf treatment                                                             Control           --         38.3   100                                        CCC               1.5        38.0   99                                                           6.0        32.5   85                                          ##STR404##       1.5 6.0    30.0 25.5                                                                             78 67                                       ##STR405##       1.5 6.0    33.0 30.0                                                                             86 78                                      ______________________________________                                    

EXAMPLE 25

Herbicidal action

The new compounds listed in Tables 1 to 3 below have proved to be effective in the control of unwanted plants. The following test method was employed.

Paraffined paper cups having a volume of 170 cm³ were filled with a sandy loam, and the seeds of the test plants sown therein, separated by species. (The species are also listed below.)

In the first group, treatment was effected immediately after sowing and before germination of the seeds (preemergence treatment=soil treatment). Shallow sown seeds not completely covered with soil came into contact with the active ingredients. In the second group, the plants were treated postemergence (=leaf treatment) at a growth height of from 2 to 8 cm, depending on the rate of growth and shape of the species concerned. The compounds were suspended or emulsified in water and applied to the aid of fine nozzles. The amounts applied are given in Tables 1 to 3. The soil and plants were thoroughly sprinkler irrigated for the duration of the experiment. The cups were placed in the greenhouse and kept in the temperature range 12°-25° C. or 18°-35° C., depending on the temperature requirements of the various species. After 2 to 6 weeks the action was assured visually on a 0 to 100 scale, 0 denoting no damage and 100 denoting plants not germinated or completely destroyed.

List of plants employed in Tables 1 to 3:

    ______________________________________                                         Latin name         English name                                                ______________________________________                                         Alopecurus myosuroides                                                                            Blackgrass                                                  Cynodon dactylon   Bermudagrass                                                Cyperus esculentus Yellos nutsedge                                             Datura stramonium  Jimson weed                                                 Digitaria sanguinalis                                                                             Hairy crabgrass                                             Echinochloa crus-galli                                                                            Barnyardgrass                                               Euphorbia spp.     Spurge family                                               usually E. geniculata                                                          Eleusine indica    Goosegrass                                                  Galium aparine     Catchweed bedstraw                                          Ipomoea spp.       Morningglory                                                usually I. lacunosa                                                            Matricaria chamomilla                                                                             Wild chamomile                                              Panicum virgatum   Switchgrass                                                 Poa annua          Annual bluegrass                                            Setaria faberii    Giant foxtail                                               Sinapis alba       White mustard                                               Solanum nigrum     Black nightshade                                            Sorghum halepense  Johnsongrass                                                Stellaria media    Chickweed                                                   ______________________________________                                    

Results (Tables 1, 2, 3)

(1) The herbicidal action of the new compounds in combatting and controlling unwanted plant growth was confirmed. This action was observed on monocotyledonous and dicotyledonous species, and with pre- and postemergence application. Representatives of widely varying botanical families were investigated.

(2) Herbaceous crop plants were not very resistant to the compounds given in Tables 1 to 3 (soil and leaf treatment). However, the compounds are suitable for removing and suppressing unwanted plants when a technique is employed in crop plants in which the active ingredients do not come into direct contact with the young leaves of the crop plants (postdirected spray, lay-by treatment, granulation of the active ingredients). It is also possible to apply the compounds to perennial species after cutting or during dormancy. A further field is weed control in woody crop plants such as berry bushes and trees of all kinds. Unwanted plants can also be removed or suppressed in loci where no account need be taken of crop plants.

                                      TABLE 1                                      __________________________________________________________________________     Herbicidal action - preemergence application                                   __________________________________________________________________________                     Application                                                                          Test plants and percentage damage                        Active          rate  Alopecurus                                                                           Cynodon                                                                             Cyperus                                                                              Digitaria                                                                            Euphorbia                                                                            Ipomoes                     ingredient      kg/ha myosuroides                                                                          dactylon                                                                            esculentus                                                                           sanguinalis                                                                          spp.  spp.                        __________________________________________________________________________      ##STR406##     2.0 4.0                                                                              -- 85 70 90                                                                               27 55 100 --                                                                               -- -- 50 60                        ##STR407##     2.0 4.0                                                                              70 83 65 90                                                                               45 60 70 100                                                                               90 100                                                                               -- 29                        ##STR408##     2.0 4.0                                                                              55 70 80 100                                                                              55 55 -- -- -- -- 0 10                         ##STR409##     2.0 4.0                                                                              40 40 83 100                                                                              0 0   100 100                                                                              90 100                                                                               78 75                        ##STR410##     2.0 4.0                                                                              80 80  90 100                                                                             0 0   68 90 65 90 78 --                       __________________________________________________________________________                     Application                                                                          Test plants and percentage damage                        Active          rate   Matricaria                                                                          Panicum                                                                             Poa Setaria                                                                             Sinapis                                                                            Sorghum                                                                             Stellaria                   ingredient      kg/ha chamomilla                                                                           virgatum                                                                            annua                                                                              faberii                                                                             alba                                                                               halepense                                                                           media                       __________________________________________________________________________      ##STR411##     2.0 4.0                                                                              95 -- 100 --                                                                              95 --                                                                              97 100                                                                              99 100                                                                             75 100                                                                              100 --                       ##STR412##     2.0 4.0                                                                              95 -- 100 --                                                                              57 --                                                                              59 65                                                                               74 100                                                                             74 78                                                                               100 --                       ##STR413##     2.0 4.0                                                                              -- -- -- --                                                                               -- --                                                                              80 90                                                                               80 95                                                                              90 90                                                                               -- --                        ##STR414##     2.0 4.0                                                                              -- -- -- --                                                                               65 --                                                                              55 100                                                                              98 --                                                                              55 55                                                                               -- --                        ##STR415##     2.0 4.0                                                                              -- -- -- --                                                                               70 --                                                                              40 100                                                                              90 --                                                                              53 50                                                                               -- --                       __________________________________________________________________________        0 = no damage                                                                100 = complete destruction                                               

                                      TABLE 2                                      __________________________________________________________________________     Herbicidal action of a new compound and comparative agents - pre- and          postemergence                                                                  application                                                                                   Application Test plants and percentage damage                                  rate  Application                                                                          Alopecurus                                                                           Echinochloa                                                                          Galium                                                                             Sinapis                             Active ingredient                                                                             kg/ha method                                                                               myosuroides                                                                          crus galli                                                                           aparine                                                                            alba                                __________________________________________________________________________      ##STR416##    1.0 2.0 1.0 2.0 4.0                                                                  PRE PRE POST POST POST                                                               0 0 70 70 --                                                                         80 90 100 100 --                                                                     -- -- -- -- 50                                                                     90 90 100 100 --                     ##STR417##    1.0 2.0 1.0 2.0 4.0                                                                  PRE PRE POST POST POST                                                               0 0 80 80 --                                                                         80 90 100 100 --                                                                     -- -- -- -- 0                                                                      60 60 100 100 --                     ##STR418##    1.0 2.0 1.0 2.0 4.0                                                                  PRE PRE POST POST POST                                                               20 78 40 50 --                                                                       100 100 98 98 --                                                                     -- -- -- -- 0                                                                      0 0  0 0 --                          ##STR419##    1.0 2.0 1.0 2.0 4.0                                                                  PRE PRE POST POST POST                                                               80 95 30 70 --                                                                       85 85 95 100 --                                                                      -- -- -- -- 50                                                                     100 100 100 100 --                  __________________________________________________________________________       0 = no damage                                                                 100 = complete destruction                                               

                                      TABLE 3                                      __________________________________________________________________________     Herbicidal action of new compounds and comparative agents -                    pre- and postemergence application                                             __________________________________________________________________________                       Application Test plants and percentage damage                                  rate  Application                                                                          Alopecurus                                                                           Datura                                                                               Digitaria                                                                            Eleusine                       Active ingredient kg/ha method                                                                               myosuroides                                                                          stramonium                                                                           sanguinalis                                                                          indica                         __________________________________________________________________________      ##STR420##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           95 95 98 25 25 30                                                                    -- -- -- 30 40 60                                                                    -- -- -- 80 80 90                                                                    -- -- -- 50 50 50               ##STR421##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           30 25 25 15 22 38                                                                    -- -- -- 95 95 100                                                                   -- -- -- 50 70 90                                                                    -- -- -- 40 50 50               ##STR422##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           68 85 98 28 38 35                                                                    -- -- -- 10 20 60                                                                    -- -- -- -- -- --                                                                    -- -- -- -- -- --              __________________________________________________________________________                       Application Test plants and percentage damage                                  rate  Application                                                                          Galium                                                                                Lamium                                                                              Poa   Solanum                        Active ingredient kg/ha method                                                                               aparine                                                                              spp.  annua nigrum                         __________________________________________________________________________      ##STR423##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           88 80 88 0 0 10                                                                      72 90 95 50 50 90                                                                    100 100 100 30 30 42                                                                 85 85 90 22 22 38               ##STR424##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           60 80 75 0 0 0                                                                       50 65 75 75 85 85                                                                    50 58 65 30 30 30                                                                    75 80 90 100 100 100            ##STR425##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           70 80 90 5 5 5                                                                       25 60 85 0 10 20                                                                     95 98 100 35 35 40                                                                   0 15 25 10 10 20               __________________________________________________________________________                       Application Test plants and percentage damage                                  rate  Application                                                                          Alopecurus                                                                           Datura                                                                               Digitaria                                                                            Eleusine                       Active ingredient kg/ha method                                                                               myosuroides                                                                          stramonium                                                                           sanguinalis                                                                          indica                         __________________________________________________________________________      ##STR426##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           70 75 90 15 38 45                                                                    -- -- -- 60 95 100                                                                   -- -- -- 60 70 80                                                                    -- -- -- 90 90 90               ##STR427##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           70 88 100 32 40 50                                                                   -- -- -- 50 60 65                                                                    -- -- -- 60 60 80                                                                    -- -- -- 60 60 70              __________________________________________________________________________                       Application Test plants and percentage damage                                  rate  Application                                                                          Galium                                                                                Lamium                                                                              Poa   Solanum                        Active ingredient kg/ha method                                                                               aparine                                                                              spp.  annua nigrum                         __________________________________________________________________________      ##STR428##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           80 100 100 10 15 20                                                                   95 95 95 60 90 90                                                                   100 100 100 35 40 50                                                                 95 95 95 85 100 100             ##STR429##       2.0 4.0 8.0 2.0 4.0 8.0                                                              PRE PRE PRE POST POST POST                                                           72 98 90 10 18 30                                                                    95 95 95 55 60 95                                                                    80 92 95 38 52 68                                                                    95 95 95 90 95 100             __________________________________________________________________________       0 = no damage                                                                 100 = complete destruction                                                     PRE = preemergence application                                                 POST = postemergence application                                         

EXAMPLE 26

90 Parts by weight of compound 1is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE 27

20 Parts by weight of compound 2 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 28

20 Parts by weight of compound 1 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 29

20 Parts by weight of compound 1 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 30

20 Parts by weight of compound 1 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

EXAMPLE 31

3 Parts by weight of compound 2 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

EXAMPLE 32

30 parts by weight of compound 2 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

EXAMPLE 33

40 Parts by weight of compound 1 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-ureaformaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in 100,000 parts by weight of water gives an aqueous dispersion containing 0.04 wt% of active ingredient.

EXAMPLE 34

20 Parts of compound 1 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

EXAMPLE 35

Further experiments were carried out in the greenhouse under the conditions described in Example 11. The plastic pots had a volume of 300 cm³. As the plants which were examined liked the warmth (Euphorbia geniculata, Arachis hypogaea, Cynodon dactylon), they were kept at from 20°-30° C. Cynodon dactylon from seed was cut once and the young growth treated postemergence. Results

Postemergence treatment with the compounds of the invention listed in Table 1 below resulted in a considerable (and desirable from the crop point of view) reduction in shoot growth in groundnuts (Arachis hypogaea) and Bermudagrass (Cynodon dactylon). The same effect can be achieved with a preemergence application, as shown for instance in Table 2 at Euphorbia geniculata. It is particularly noteworthy that the comparative agents only act on certain plant species. By contrast, the compounds according to the invention act on a larger number of plant species. Similar effects were obtained with the new compounds in soybeans (Glycine max.), Indian corn (Zea mays) and other species.

                                      TABLE 1                                      __________________________________________________________________________     Growth-regulating action in groundnuts (A. hypogaea) and Bermudagrass          (C. dactylon) - postemergence application in greenhouse                                         Application                                                                          Test plants and growth height                                            rate  Arachis hypogaea                                                                        Cynodon dactylon                               Active ingredient                                                                               kg/ha cm  relative                                                                            cm   relative                                  __________________________________________________________________________     Untreated control                                                                               --    16  100  11   100                                        ##STR430##      2.0 1.0 0.5                                                                          9 12 13                                                                            56 75 81                                                                            4 4 4                                                                               36 36 36                                   ##STR431##      2.0 1.0 0.5 0.25                                                                     5 7.5 8 8                                                                          31 47 50 50                                                                          3 4 4 --                                                                           27 36 36 --                                ##STR432##      2.0 1.0 0.5                                                                          10 14 14                                                                           62 87 87                                                                            6 6 7                                                                               54 54 64                                   ##STR433##      2.0 1.0 0.5                                                                          -- -- --                                                                           -- -- --                                                                            6 7 8                                                                               54 64 73                                   ##STR434##      2.0 1.0 0.5 0.25                                                                     7 7 8 9                                                                            44 44 50 56                                                                          9 12 12 --                                                                         82 109 109 --                             prior art                                                                      [ClCH.sub.2CH.sub.2N(CH.sub.3.sup.⊕).sub.3 ]Cl.sup.⊖                                2.0   14  87   9    82                                                         0.5   16  100  9    82                                        prior art                                                                      __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                         Growth-regulating action in Euphorbia geniculata - preemergence                treatment in greenhouse                                                                               Test plants and                                                          Appli-                                                                               growth height                                                            cation                                                                               Euphorbia                                                                rate   geniculata                                             Active ingredient  kg/ha   cm       relative                                   ______________________________________                                         Untreated control  --      11       100                                         ##STR435##        1.0 0.5 0.25                                                                           3 5 6    27 45 54                                   [ClCH.sub.2CH.sub.2N(CH.sub.3.sup.⊕).sub.3 ]Cl.sup.⊖                                  1.0     9        82                                                            0.5     10       91                                                            0.25    10       91                                         prior art                                                                       ##STR436##        1.0 0.5 0.25                                                                           10 12 12 91 109 109                                 prior art                                                                      ______________________________________                                     

We claim:
 1. A polycyclic nitrogen-containing compound of the formula ##STR437## where A denotes the radical --N═N--, B denotes the radicals --SO₂ --, ##STR438## and --S--, C denotes the radicals --N═N-- or ##STR439## n denotes one of the integers 0 and 1, m is 1, and R¹ is linked to B through O or N and denotes radical --OAlk(Ar), the radical ##STR440## or --N(Alk,Ar)₂, Alk denoting alkyl and Ar denoting an aromatic radical and R² and R³ are identical or different and each denotes (B)_(m) --R⁴, R⁴ having the same meanings as R¹, and salts of these compounds.
 2. A process for reducing crop plant growth height wherein the crop plants or the soil are treated with an effective amount of a polycyclic nitrogen-containing compound of the formula of claim 1 to reduce crop plant growth height.
 3. A polycyclic nitrogen-containing compound as set forth in claim 1, wherein R¹ is linked to B through O.
 4. A polycyclic nitrogen-containing compound as set forth in claim 1, wherein R¹ is linked to B through N.
 5. A process for reducing crop plant growth height wherein the crop plants or the soil are treated with an effective amount of a polycyclic nitrogen-containing compound as set forth in claim 3 to reduce crop plant growth height.
 6. A process for reducing crop plant growth height wherein the crop plants or the soil are treated with an effective amount of a polycyclic nitrogen-containing compound as set forth in claim 4 to reduce crop plant growth height. 